Microbial transformation of cannabinoids. I. Metabolism of (–)-Δ⁹-6a,10a-trans-Tetrahydrocannabinol by Chaetomium globosum

Abstract

Chaetomium globosum isolated from Cannabis sativa plant material converts (-)-Δ⁹-6a,10a-frans-tetrahydrocannabinol (Δ⁹-THC) (1a) into a number of metabolic products, which include the 3'-hydroxy, 11-hydroxy and 3',11-dihydroxy derivatives (1c), (1b) and (1d) respectively. The structure of the 3'-hydroxy-Δ⁹-THC (1c) has been confirmed by synthesis, whilst the structure of the 3',11-dihydroxy-Δ⁹-THC (1d) follows from mass spectroscopic comparison with the 3'-hydroxy and 11-hydroxy derivatives.